The Official Preppy Handbook was originally released in 1980 and has since been updated, but Gomez could school the blue-blooded set on how to do casual style. Gomez swapped out the twinsets for a modern tonally coordinated topper and bodysuit. Pleated khakis received a downtown makeover through designer Nicolas Ghesquière’s luxe jeans, while penny loafers were given a dose of high-fashion flair from Tod’s. And the final touch? Tortoise-shell shades were exchanged for rock star friendly round sunnies.